Everything Changed This Year
A lot has changed lately — some planned, some not.
We made a few big decisions, welcomed another tiny human, and found ourselves rethinking what the next chapter looks like for our family.
For now, we’re trading slip fees for open roads, slowing things down, and giving the kids time to grow while we figure out what comes next. The boat dream isn’t gone — it’s just on pause.
This video is a quick life update and a look at where we’re headed (and why).
#VanLife #sailing #boat
▬ Support Us! ▬
We just started a Patreon to get our journey started!
Throw us a bone @ https://www.patreon.com/RoamingRupps
We share more of our daily lives on our Instagram stories, so give us a follow!
Ashley: https://www.instagram.com/ashley_crompton
Colin: https://www.instagram.com/sailorcolin
A lot has changed lately — some planned, some not.
We made a few big decisions, welcomed another tiny human, and found ourselves rethinking what the next chapter looks like for our family.
For now, we’re trading slip fees for open roads, slowing things down, and giving the kids time to grow while we figure out what comes next. The boat dream isn’t gone — it’s just on pause.
This video is a quick life update and a look at where we’re headed (and why).
#VanLife #sailing #boat
▬ Support Us! ▬
We just started a Patreon to get our journey started!
Throw us a bone @ https://www.patreon.com/RoamingRupps
We share more of our daily lives on our Instagram stories, so give us a follow!
Ashley: https://www.instagram.com/ashley_crompton
Colin: https://www.instagram.com/sailorcolin
Roaming Rupps
Hi Friends! We are Ashley & Colin. Join us as we modernize this Beneteau Oceanis 500 in hopes to become liveaboards! Please subscribe as we try to post weekly videos.
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Roaming Rupps Lastest Videos
Everything Changed This Year
A lot has changed lately — some planned, some not. We made a few big decisions, welcomed another tiny human, and found ourselves rethinking what the next chapter looks like for our family. For now, we’re trading slip fees for open roads, slowing thing...
Saying Goodbye to the Bahamas ⛵ Storms & Surprises Ahead!
We wrap up this season’s Bahamas adventures with a dramatic exit! Cold fronts are rolling through and the squalls just won’t stop, forcing us to change our course. Instead of making it all the way to Jacksonville, we’re faced with tough decisions and...
My wife and child left me | #Hurricane season in the #Bahamas
In today's video, Ashley and Fleix make their way back to the States. Colin hunkers down for some serious squalls before a new crew arrives to sail the boat back to the States. #hurricane #bahamas #liveaboard #family Read more about today's vlog and our ...
They left me. #sailing #boating #bahamas #hurricane
Read more about today's vlog and our #sailing adventure on our site! https://roamingrupps.com/ ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our daily ...
Hope Town, Abacos: Cruisers Tips, Tricks & The Golf Cart We Didn’t Need
In today’s vlog, we sail into Hope Town, Abacos, to ride out a blow, stock up on provisions, and share our best tips for visiting this charming Bahamian town. But the day takes an unexpected turn when we’re manipulated into renting an unnecessary golf ...
Hope Town Tips & The Golf Cart We Didn’t Need 🚤🇧🇸 #hopetown #abacos #bahamas
We sailed into Hope Town, Abacos, to ride out a blow, grab some provisions, and share our top tips for visiting. But instead… we got stuck renting a golf cart we didn’t need after finding the grocery store closed for good. Add in a last-minute visa run...
Egg Island to Hope Town: A Calm Start… Then It Got WILD!
We set sail from beautiful Egg Island with hopes of a peaceful anchorage—but Mother Nature had other plans. With rolling anchor conditions and dark skies closing in, we made a split‑second decision: head for the safety of Hope Town in the Abacos. Read...
Calm sail to the #Abacos! #eleuthera #liveaboard
Read more about today's vlog and our #sailing adventure on our site! https://roamingrupps.com/ ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our daily ...
What its like to run aground in the #Bahamas #eleuthera #boatlife
In our recent vlog, we go through the process where you put a little too much trust in the locals. ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of our da...
Goodbye #Eleuthera: Devil’s Backbone, Shallow Water Drama, Gorgeous Anchorages
We finally said farewell to #Eleuthera—but not before taking on the legendary Devil’s Backbone. With a local pilot guiding us through the razor-thin shallows, we made our way off the island and into some of the trickiest water we’ve seen yet. Spoiler...
Off the Grid in Eleuthera: Caves, History, and Hidden Roads
In today’s vlog, we explore abandoned Navy bases, visit the stunning #CathedralCaves, and take a scenic drive across #Eleuthera. #bahamas ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon....
Locked Out by Disney: What Happened to This Bahamian Beach?
Today, we finally stepped off the boat to explore one of our favorite spots in the Bahamas—only to find out we couldn't get there. What used to be a peaceful, easy-to-reach beach has now been taken over by Disney. We were shocked to discover restricted a...
Devil’s Backbone: Spanish Wells to Harbour Island (Why You NEED a Pilot!)
The Devil's Backbone is no joke! Watch us navigate this challenging reef passage from Spanish Wells to Harbour Island. We hired a pilot for $100; it is cheap insurance and calmed our nerves. See the stunning but dangerous beauty of this route. #Caribbean #...
Sneak preview of our Devil’s Backbone Vlog! #liveaboard #sailing #bahamas
See why why decided to hire a pilot to help us navigate the coralheads and reefs from Spanish Wells to Harbour Island via the Devils Backbone. ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patre...
Sailing to Meeks Patch: Bonfires, Beach Bliss & a Freezer Fail
Join us as we set sail from Royal Island to the beautiful Meeks Patch! We have the entire beach to ourselves for a perfect beach day, let the dogs run free (while dodging the island’s famous wild pigs), and soak in the peaceful cruising life. But, of cou...
Sailing to Spanish Wells: Abandoned Getaway, Stormy Weather & Snake Trouble!
In today’s adventure, we set sail from Rose Island to the charming Spanish Wells, navigating beautiful Bahamian waters with our little crew! We spend a few days catching up on boat life chores, riding out a storm, and exploring an abandoned island hideaw...
Berry Islands to Nassau Madness, a 15HP 2-Smoker… & Finally Relaxing!
Join us on another real-life Bahamas cruising adventure! We make the jump from the Berry Islands to Nassau, where things get a little crazy! From the hustle and chaos of Nassau to navigating busy waters, we also pick up a 15HP Yamaha 2-stroke to add some e...
Bahamas Cruising Gone Wrong? Bimini to Berry Islands & Riding Out a 40kt Blow!
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Can We Jump to Bimini before Disaster Strikes?
In this weeks video we make the jump to #Bimini #Bahamas and hit a few road blocks along the way. #sailing ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a bone @ https://www.patreon.com/RoamingRupps We share more of...
Testing our Relationship in New Smyrna | Sailing 42
In this week's video, we test our relationship with a broken shifter cable during anchoring and make our way to Cape Canaveral. Read more about today's vlog and our #sailing adventure on our site! https://roamingrupps.com/ ▬ Support Us! ▬ We just s...
Cumberland Island to St Augustine | Sailing 41
In today's vlog we #sail our way south and stop at some great locations. We also get a little bit of help from https://www.instagram.com/sailingisabela/ before we jump into #Flordia. #sailing Read more about today's vlog and our #sailing adventure on o...
Quick Trip to Cannes to See Some Yachts and Excess Catamarans
Come with me as Colin takes a quick trip to Cannes to see the boats how and visit the #Excess Catamaran factory. $50 hotel - https://maps.app.goo.gl/o2Y6MXqKG77GoV7x7 ▬ Support Us! ▬ We just started a Patreon to get our journey started! Throw us a...
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